Living a More Purposeful Life One Cent at a Time

Are Side Hustles Still Stupid?

To celebrate my move to the Sweet 16 spot in the Rockstar Finance Rumble, I thought I would update this post with a few more bloggers and their takes on side hustling. Hop down to the bottom to see the full list!

Last year, I boldly declared the stupidity of the side hustle. I didn’t expect what could easily read as an affront to a darling of the personal finance community to go over well. It definitely wasn’t in line with the whole “if you don’t have anything nice to say, don’t say anything at all” mentality (sorry, Mom!). Little did I know, though, that the post would resonate with bloggers and readers so much so that I’ve managed to make it through the first few rounds of the Rockstar Finance Rumble. All of this hoopla (Can I call it hoopla if it’s me re-reading my own post twice?) has got me wondering something: Do I still think side hustles are stupid?

The Glitz of the Hustle

It’s not sweat that you see. No, no. That’s a side hustler glistening. When I read incredible debt payoff posts (or write them and toot my own horn!) or serendipitous stories of side hustles that just fall into someone’s lap (like Jane from Cash Fasting and her incredible and unexpected hustle), I can see the glisten. Truly, I can.

Multiple income streams are powerful. They pay down debt. They open doors. They can lead to cash, career moves, and confidence. In my experience, though, they’re also a lot of work and aggravation.

The State of My Side Hustles

On the surface, my side hustles are going well. But that’s the surface. Take writing for instance. I am officially a professional writer. BOOM! But of the handful of freelancing gigs that I have, only one pays very well and regularly. I have made thousands of dollars re-selling all of the nonsense I never should have bought on Poshmark and Tradesy and ThredUp and local sites (oh my!). But I have also watched these sites take a bigger and bigger piece of the money pie over time. Not to mention the creepy encounter with a foot fetishist on Poshmark. Then, there’s tutoring. It’s an extension of my passion. It’s also a great way to get sick.

Perhaps the problem is that I haven’t found the perfect side hustle. Or perhaps the problem is that it doesn’t exist.

A Request & Some Recommendations

If you would be so kind, consider voting for my post (“Hustle) in Game 7 of the Rockstar Finance Rumble. But before you vote “Hustle”, I would be remiss if I didn’t also tell you to scope out the competition. So, make sure to swing by the post by Matt at Optimize Your Life.

And if you’re looking for some other thoughts on side hustles, check out these links:

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29 Comments

I’m thinking the perfect side hustle doesn’t exist, in large part because it’s something that’s added on to an already full plate. Time is scarce, and even the very best side hustle takes away from that.

That is exactly my current struggle. It’s a terrible (and terribly sad) thing to say, but I’m absolving myself by telling myself that HP won’t remember his first year anyway. By continuing to side hustle now, it theoretically will allow me to be more present when he is a bit older. What a struggle.

The problem with side hustle is that it take some of your time that you have after your primary job. At least you could get extra money but you need to find the right balance between everything (free time, hobby, side hustle, primary job, family …)

Yes! Perhaps if I found a side hustle that was more passive. I think it’s particularly challenging when it’s a side hustle that requires you to be away from home (if you’re trying to find more family time anyway!).

Exactly my thoughts. Side hustles are worth it if they are scalable. If the only hustle you can rustle up involves trading time for money indefinitely, then it will contribute to burnout. The exception to this may be a true passion project.

We all have 168 hours per week, so if we only work 40, we’re missing out on a lot of potential earning hours. If you’re in a job with overtime potential, even 10 more hours typically pays 1.5x or the equivalent of 15 hours. That’s a 37.5% bump in pay!
But many of us don’t have such an opportunity with our current jobs, so we seek to replicate that in a way that allows us to be our own boss. Except after a while you realize you’re still not your own boss, the client is.
My side hustle for 3+ years has been Uber. I stopped driving on the platform and now only take trips for people who contact me directly, but even that has drawbacks and very low volume. For example, I was supposed to have a ride last night at 7pm that would have had me home by 9. Unfortunately the flight was delayed by 2.5 hours and I didn’t get home until after 11. Was the $85 nice to have? Absolutely. Was it worth losing my whole evening? Meh.

Figuring out what your time is worth is key. I have to keep reminding myself of this when I see opportunities to freelance that pay $10-$20 an hour. Between taxes and time away from my family, I just can’t say yes to that.

I don’t think the perfect side hustle exists. Some are better than others, but nothing in life is perfect. The art of the side hustle is beautiful in the way that you can come on go as you choose with most side hustles as you need the additional funds.

Once your side hustle evolves to the point where it is taking up as much time as your full time source of income, it is no longer a side hustle, in my opinion.

Having multiple side hustles is a great idea as long as they don’t engulf too much of your time. It allows you to diversify your income streams and gives you flexibility to earn income in different areas as the markets change.

Side hustling certainly isn’t for everyone, but if you find something that works for you, it can be a great way to earn yourself some extra cash.

So I admit I love a good side hustle…because I don’t work! Then they are awesome. A little bit of cash. Some grown-up time. Personal growth. A new challenge. It’s great! Well, let me add, neither Adam or I work! But, yeah, when we had real jobs, like real grown-ups, it was a total grind and I hated almost every minute. Even buying and renovating our rental properties was a miserable grind on top of a 45 hour a week job. Now those properties are awesome. But not at first.

I think it’s cool that you are trying to keep grinding it out. But you don’t have to find it glittery. It just isn’t on top of real jobs.

Sure. Rub it in, Jillian! Just kidding! Actually, you make an excellent point (duh). It’s why I have such a hard time saying no to things over the summer. I’m not working nearly as much, so it seems like more time to say yes.

I am a big, big advocate of the side hustle. I had one, and then I got my dream job and let the side hustle slide, neglecting it almost completely while I put in long hours at my day job (for no overtime, because salaried). Then one day, out of the blue – BOOM, laid off without warning. And I didn’t have my side hustle there to fall back on. Had to take on a new freelance gig that paid less than unemployment because I was starting from scratch (and reduced the unemployment that I got, so I ended up with less than I could live on, as the primary breadwinner) and then take a full-time job that wasn’t a great fit.

It was the suck and I the whole time I was wishing that I’d kept up my side hustle so that I would A) have the extra cash from it for a better cushion (I had an emergency fund, but was digging into it hard to supplement the unemployment) and B) could have ramped it up to full time when I was laid off.

1.5 years and 2 bad-fit jobs later, I was laid off again from the second bad-fit job. But that time, I’d kept the freelance work from my unemployment going for that whole time period. So the very next morning after layoff #2, I just went to my freelance client and said “Hey, I got laid off! So I’m available for full time work if you’ve got it for me.” And they did. So I ended up with a new dream job, and didn’t miss a single working hour between layoff and new job. Because I maintained a side hustle.

Now, I strongly believe in the power of a side hustle as a safety net, a parachute. I refuse to live without one until I’m completely financially independent.

I get that, Stephonee. As someone who was fired unexpected twice (with a teaching contract!), side hustles are helpful. It sounds like you have used yours to make all the right moves in bad situations! I dream of passive extra income streams, though. Peace of mind comes in many forms. Having extra income security is nice. So is free time and sanity.

I have a bit of a love hate relationship with side hustles. I don’t like just how random it is to have a good month vs a bad month income wise. For instance, as a pet sitter, I made a truckload of money over the last Christmas. This month not so much because everyone is at home. It’s a bit frustrating but I guess that’s downside.
I also tutor a bit on the side and love it, so I can resonate with you on that one!

First off, I LOVED your original post about the stupidity of side hustles. It is a lot to put on your plate when you already spend 35-50 hours a week at a day job. I will also be the first to say that I am in a perfect position to side hustle and so I do, but I am single and don’t have children. I don’t need to make those tradeoffs as much as you might, and I love and admire how much you protect your family time!

I have found as close to the perfect side hustles as I think you can get (and they are based on teaching so we should totally discuss!) Some of my main criteria were that the side hustles had to be a) online b) flexible (yes, there are deadlines but I can work more or less when I want) and c) pay well (for me, this is around $30+ an hour). Otherwise, it’s just not worth my time, energy, sanity!

What appeals to me about side hustles are my increased options. I have enjoyed the extra money and the pleasure of developing new skills. Building a talent stack means I know I’ll be able to continue making money if something happens to my main income source.

That said, balance is important. It’s easy to get burnt out. Very true about the germs, too – I work with toddlers in one of my side hustles, and I won’t see children who are sick. Just not worth it to me to take that chance.

It was nice to read the other posts you linked to. Our Next Life’s post on how teaching yoga is like MLM was thought provoking.

I am still struggling to find some side hustles really. I am not skilled to do anything freelance wise and so this limits me alot! I’d love some side hustle ideas or links to posts you’ve already done about them? I’m new to your blog so just finding my way around.

Life is too short to while it away doing things you don’t love. If you love what you are doing either professionally or as a side gig, keep doing it. If you don’t try something else. In my experience money is very easy to make, but incredibly hard to hold on to. It may be that the best side hustle is just figuring how to hold on to it better.

Have to say I’ve never found the perfect side hustle for me….maybe one will pop up but I’m not too bothered either way. I appreciate the simplicity and hassle-free ness of no side-hustles, and I can use my free time volunteering instead, which bring me feel good points rather than cold hard cash.

I love me some side hustles. My actual job is being a mom, but I string a bunch of side hustles together to make some sort of income. I love my babies, but the side hustles keep me sane and working toward something for myself.
I can see how it wouldn’t be for everyone though. My family members always talk about starting their own when they see me working but they have yet to actually do it!

My weekend job is still new enough that the shine and novelty haven’t worn off yet. And it’s well-paying as far as part-time jobs go. But I’ve been working a lot lately and I am just tired. It’s a lot. I’ve promised myself that when the weather gets nicer I won’t sign up to work every weekend like I am now so I can prioritize things like hiking. Sure I’ll miss the extra money but I bet having an actual two-day weekend (instead of one or zero days) is going to feel great, too.

I find that the amount of money that side hustles bring in is rarely worth the time that they take up. Also, I’ve had a whole bunch of them, so what do I know?

I did recently quit one of my side hustles after dialing back the others. Now I’m at maybe two hours a month on the side. I’ll probably pick some more work up in the future, but for now, I’m enjoying my time.

Also, I don’t want to go up against you in the next round. (Although I like that both of our articles are going against the grain of the PF community.)